Use of 2-aminoprop-1-ene-1,1,3-tricarbonitrile for the synthesis of tetrahydronaphthalene, hexahydroisoquinoline and hexahydrocinnoline derivatives with potential antitumor activities

Mohareb, Rafat M.; Moustafa, Hosam E.

doi:10.2478/v10007-011-0001-y

Cited by 7 publications

(2 citation statements)

References 16 publications

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“…[34] At this step, polyethylene glycol can help speed up the reaction by forming hydrogen bonds. By two attacks of nitrogen atom on nitrile group and passing through intermediate (C), [35] intermediate (D) is formed, which subsequently converts to the desired product (4) through 1,3-H shift. When malononitrile is used instead of enamine, spiro-dihydropyridines derivatives are synthesized by a similar mechanism.…”

Section: Resultsmentioning

confidence: 99%

One‐Pot Multicomponent Synthesis of Novel Spiro‐(1,8)‐Naphthyridine Derivatives in PEG‐400

Asilpour,

Saberi,

Hasaninejad

2023

ChemistrySelect

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A one‐pot multi‐component pathway is reported to synthesize novel spiro‐(1,8)‐naphthyridine derivatives in good to excellent yields via the condensation reaction of isatin derivatives, malononitrile dimer and enamine derivatives. In polyethylene glycol‐400 at 80 °C, more than 30 novel products of spiro‐(1,8)‐naphthyridines were synthesized up to 95 % yields with only water as a by‐product. Separation of the products was performed efficiently and no additional operation was needed for purification of the products, except that, in some cases, recrystallization was done. Moreover, some new spiro‐dihydropyrimidines were efficiently synthesized when malononitrile (or methyl/ethyl‐2‐cyanomalonate) was employed instead of enamines.

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Section: Resultsmentioning

confidence: 99%

One‐Pot Multicomponent Synthesis of Novel Spiro‐(1,8)‐Naphthyridine Derivatives in PEG‐400

Asilpour,

Saberi,

Hasaninejad

2023

ChemistrySelect

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“…Many cinnoline derivatives (Figure 39) such as 9-substituted-4,10-dimethylpyrano[2,3- f ]cinnolin-2-ones with N -piperazinyl moieties at C-9 73 [84] , 6-substituted-4-methyl-3-(4-arylpiperazin-1-yl)cinnolines 74 [85], hexahydrocinnolines 75 [86] and pyrazolo[4,3- c ]cinnoline derivatives 76 [87] were synthesized and evaluated in vitro for their antitumor activity against breast cancer cell lines MCF-7 and MDA-231 for bicinnolines 77 [88].…”

Section: Biological Activity Of Cinnoline Derivativesmentioning

confidence: 99%

Cinnoline Scaffold—A Molecular Heart of Medicinal Chemistry?

Szumilak

Stańczak

2019

Molecules

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The cinnoline nucleus is a very important bicyclic heterocycle that is used as the structural subunit of many compounds with interesting pharmaceutical properties. Cinnoline derivatives exhibit broad spectrum of pharmacological activities such as antibacterial, antifungal, antimalarial, anti-inflammatory, analgesic, anxiolytic and antitumor activities. Some of them are under evaluation in clinical trials. In the present review, we have compiled studies focused on the biological properties of cinnoline derivatives conducted by many research groups worldwide between 2005 and 2019. Comprehensive and target oriented information clearly indicate that the development of cinnoline based molecules constitute a significant contribution to the identification of lead compounds with optimized pharmacodynamic and pharmacokinetic properties.

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Synthesis of Some New Polyfunctionalized Pyridines

Amer

2017

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).5-Methyl-2,4-dihydro-3H-pyrazol-3-one and/or 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one was reacted with arylidenemalononitrile in the presence of sodium alkoxide to give 2-amino-6-alkoxy-4-arylpyridine-3,5-dicarbonitrile 4a-e instead of the reported pyrazolo[3,4-b]pyridine-5-carbonitriles. The same products 4a-e were prepared via reaction of arylidenemalononitrile with sodium alkoxide in an appropriative alcohol. However, the new synthetic route for preparation of their positional isomer 4-amino-6-alkoxy-2-arylpyridine-3,5-dicarbonitrile 7a-j has been achieved via reaction of 2-aminoprop-1-ene-1,1,3-tricarbonitrile with different aromatic aldehydes under the same conditions.

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Use of 2-aminoprop-1-ene-1,1,3-tricarbonitrile for the synthesis of tetrahydronaphthalene, hexahydroisoquinoline and hexahydrocinnoline derivatives with potential antitumor activities

Cited by 7 publications

References 16 publications

One‐Pot Multicomponent Synthesis of Novel Spiro‐(1,8)‐Naphthyridine Derivatives in PEG‐400

One‐Pot Multicomponent Synthesis of Novel Spiro‐(1,8)‐Naphthyridine Derivatives in PEG‐400

Cinnoline Scaffold—A Molecular Heart of Medicinal Chemistry?

Synthesis of Some New Polyfunctionalized Pyridines

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